The point at which your interviewer asks you to share your greatest weakness is the portion of a job interview that you dread most, and for good reason: Lame answers like "I'm a perfectionist" or "I care too much" are well-worn clichés, but how can you intelligently answer that question? Developer and blogger Ash Moran offers this thoughtful approach.

Humans are creatures of habit, and creatures of ritual. These habits and rituals are comforting to us, and give a sense of structure to our lives and how we behave. But these rituals can crystallise, and we often work through them so religiously and mechanically that to an outsider it might well appear that the ritual works us through it, rather than the reverse. Sometimes they can take on a distinctly pathological character, as thinking about the true purpose of the activity stops, and the ritual starts serving some other end.

One activity I believe is in danger of being so far ritualised, if it hasn't been already, is the job interview. This is generally structured as being beckoned into a room with several (relatively) senior staff members. They will shake your hand, the purpose of which is usually to determine your chances of defeating a stone crab in an arm wrestling contest. Then there is a brief moment where the interview panel forms 90% of their opinions about you. After a short pause, when any awkward smiles have subsided, and it has been confirmed that you are not, in fact, a hipster, the panel launches into the main event: the questions. Now the focus is squarely on the least important person in the room: you, the candidate.

The questions

The questions start innocently enough, usually with something mundane and autobiographical. In the modern era, this often requires you to recall the order you listed the events of your life on LinkedIn. But as the questions unroll, progress through the interview begins to resemble a life-threatening run through an increasingly deadly gauntlet. You may be faced first with the leg-piercingly sharp but nevertheless predictable floor spikes of What do you know about our company? No sweat! You read the company website, after all. You do know they're in the insurance business, right?

A little further down the platform you encounter a pair of menacing swinging axes, out of sync and leaving perilously little opportunity to slip through. What else is engraved on them but Why do you want to leave your current job? Restrain yourself with the negatives, build up the positives (just enough!) and… dive right through!

Almost at the end now, just one more challenge. What's this in front of you? A cold sweat breaks out on your brow. Before you rotates a giant wooden column, from which swing deadly morning stars, interspersed with serrated blades that leap out at all heights. The sound of cold, hard steel slicing the air makes you weak at the knees. You've reached: The Death Column of What Is Your Greatest Weakness?

The man behind the curtain

It's at the point of What is your greatest weakness? that I believe most interviews unhinge from reality. Because, as quality guru W Edwards Deming pointed out decades ago: most variation is in the system, and a bad system will defeat a good person every time.

To ask what an individual's greatest weakness is during an interview to decide whether they should join an organization is nonsense. The candidate will have many strengths and weaknesses, but the only ones that matter are the ones that become relevant once he is embedded as an employee in his new team. He may think his greatest weakness is that he's too shy, which may be of no consequence if he'll be working on his own a lot, or if the team includes an especially empathic and nurturing colleague already. Another candidate may feel she's unduly prone to procrastinate. But again, this may not be a problem at all, because she'll be joining as a developer in a team that pair-programs extensively and is extremely diligent about daily standups. Quite likely something completely unexpected will turn out to be a problem. The interviewer thinks: did we remember to mention that the team is all Chinese and only half of them speak English?

A case of unexpected situational weakness happened to me recently. I'd been discussing doing some management work at a company, where I expected to mainly be dealing with process matters. Determining appropriate metrics, ensuring team members were communicating the right information, focusing test coverage across existing code – these were things on my mind. Then as the conversation progressed, it became apparent I might have to lead by example with some practices. I became acutely alert—this is a .Net shop! As of writing this, I haven't worked in a .Net shop for several years, and while I know some C#, I'm in no way qualified to demonstrate the latest testing techniques to an inexperienced team. Suddenly, something that had not been even a slight concern to me for over four years—my knowledge of .Net—presented the risk of being a major weakness.

As it happens, further discussion established that my rustiness with .Net tooling wasn't a problem. I wouldn't be needed to demonstrate technical mastery to achieve a useful purpose. And there would be, in any case, people on hand with more knowledge of this while I take the time to learn. But it drove home a real risk in my current skill-set that could become a weakness in future situations similar to this.

Your weakest link

The level you achieve as you try to winch up the obstacles in your new job will be determined, just as with a physical chain, by your weakest link. But the work in a software company (Ed.: in most jobs, in fact) is no simple cargo-hauling. It's complex work: you need a repertoire of skills, you need to know when to play them, and you must realise that everybody else in the team is doing the same. So your weakest link will be determined as much by the system you're in as anything about you personally.

Your weakest link may well be hidden from you, simply by the filters you use to see the world. As Goldratt pointed out in The Choice, one of the biggest obstacles to thinking clearly is believing that we know. This is not any individual's fault. As humans, we are innately subject to a long list of cognitive biases. For the case in point, we all seem fairly well shielded from the reality that our weaknesses are brought out more by the systems and situations in which we find ourselves than problems inherent in each of us. For all the motivational posters and exhortations of "there is no I in TEAM", we still subconsciously take an analytic, reductionist attitude to the world. If we didn't, we wouldn't be asking questions like What is your greatest weakness?

A disclaimer is needed here, as it's not always the case that the system creates the weakest link. There still exist some people, who are so spectacularly anti-social, so spectacularly arrogant, so spectacularly lazy, or so spectacular in some other special way, that they will become the weakest link in almost any situation. I'd be very surprised if more than one in twenty people in an organisation fell even close this category, however. They do exist, but they are the exception to the rule. The rest are merely in the wrong place.

Time to ask for your money back

The astute reader may have noticed that by this point I haven't actually described how you should answer the question What is your greatest weakness? The reason is that to do so would be to commit a subtle failure of logical dogfooding: the "correct" answer will be determined more by your situation that anything about the question itself.

The questions you hear in an interview will reveal a lot about the mindset of the organization. While they are mercifully rare, some firms do run interviews like the gauntlet described above—the principle being that they hire anyone who makes it out alive. If so, it's likely that they're primarily testing your ability to dodge flying blades. Maybe a clever twist on the (vomit-inducing) "I'm a perfectionist" or the (mutually destructive) "I'm a workaholic, I never go home on time", is what they want: after all, there will be many more knives coming your way if you land the job.

Far more likely—and you should always apply Hanlon's Razor—is that the questions have been merely cargo-culted in from the pool of ritual questions. The interviewer may have recently read the latest "Top 20 Questions to Ask in An Interview" posts. In this situation you have more hope. If you are dealing with genuine and intelligent people, being able to move from a me! me! me! perspective to a system-level perspective could well make you shine out from the crowd, as this mindset is currently still rare. Equally, the biases and filters could kick in, and you might just blur into the background.

The problems with many interview questions run very deep, flowing from our mindset of ritual reductionism. The ideas here may not be immediately useful to you in an your next interview situation, but hopefully they will let you challenge the basis of these questions by seeing the systems involved. If you'd like to learn more about this mode of thinking, I highly recommend Goldratt's The Choice, which is specifically written about thinking clearly in everyday problems like this. (This is not an affiliate link).

Thanks for reading

Do you agree? Do you disagree? How have you seen people's actual weaknesses play out, compared to their professed ones? Maybe you have a lot of experience as either a hirer or hiree, and have an opinion on this question, or others.

If you have any thoughts, I'd love to hear them. I'm sure many people reading this have more experience on one side of this fence or the other.